title: An Ireland-Claisen approach to beta-alkoxy alpha-amino acids.
abstract: A diastereoselective Ireland-Claisen approach to beta-alkoxy alpha-amino acid esters is reported. Amino acid esters of enol ethereal allylic alcohols undergo facile syn-selective [3,3]-sigmatropic rearrangement via silyl ketene acetals. Substrate synthesis, rearrangement development, stereoselectivity, and product elaboration are discussed.
authors.affiliation: Department of Chemistry, University of Bath, Bath, UK.
authors.forename: James P
authors.initials: JP
authors.lastname: Tellam
authors.forename: Gabriele
authors.initials: G
authors.lastname: Kociok-Köhn
authors.forename: David R
authors.initials: DR
authors.lastname: Carbery
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000438:Alcohols; D000596:Amino Acids; D004952:Esters; C059688:alkoxyl radical